Water → 4-{2-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847069노트

반응식

HRID 1847069 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]=2[N:13]=1.I[CH2:15][CH2:16][C@@H:17]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:22][C:19]1([CH3:23])[O:18][C@H:17]([CH2:16][CH2:15][N:8]2[C:9](=[O:12])[CH:10]=[N:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:13][C:7]2=3)[CH2:21][O:20]1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 39871826(4R)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolaneHCID 667398036-Methoxypyrido[2,3-B]pyrazin-3(4H)-one

생성물 1

HCID 867249934-{2-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one수율 100.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

In N,N-dimethylformamide (40 ml) were dissolved 6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (1.48 g, 8.34 mmol) and (4R)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane (3.20 g, 12.51 mmol). Cesium carbonate (3.81 g, 11.68 mmol) was added to the solution and the mixture was stirred at 50° C. for 13 hours. After cooling in the air, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 2.55 g (100%) of the title compound in the form of a light yellow oily product.

후처리

  1. additionwas added to the reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-af4433c2f85a4e13beae1dd6783ded9d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952010B2

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